Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity

Yuan, Haosen; Guo, Zhixian; Luo, Tuoping

doi:10.1021/acs.orglett.6b03779

Cited by 35 publications

(33 citation statements)

References 55 publications

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“…Synthetic utility of Miura‐Murakami's method was successfully demonstrated by the total synthesis of (+)‐lysergol, as reported by Luo et al. in 2017 [Scheme (a)] . Cao et al.…”

Section: Approach To 34‐fused Tricyclic Indoles Based On the Synthesmentioning

confidence: 89%

Synthetic Methods for 3,4‐Fused Tricyclic Indoles via Indole Ring Formation

2018

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3,4-Fused tricyclic indole frameworks are found in various bioactive natural products and pharmaceuticals. The development of an efficient synthetic method for this structural motif has therefore attracted attention in the field of synthetic organic chemistry and medicinal chemistry. Herein, we summarize recent advances in the synthesis of 3,4-fused tricyclic indoles. This class of synthetic methods can be roughly classified into two categories: methods using functionalized indole derivatives as starting materials to construct a fused medium-sized ring (Types A-D: Category I), and methods of constructing a 3,4-fused tricyclic indole skeleton via indole ring formation (Types E-G: Category II). In this focus review, synthetic methods for 3,4-fused tricyclic indoles classified as Category II methods are highlighted, following a brief overview of the Category I methods. 2 3 4 5 6 7 8

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“…Synthetic utility of Miura‐Murakami's method was successfully demonstrated by the total synthesis of (+)‐lysergol, as reported by Luo et al. in 2017 [Scheme (a)] . Cao et al.…”

Section: Approach To 34‐fused Tricyclic Indoles Based On the Synthesmentioning

confidence: 89%

Synthetic Methods for 3,4‐Fused Tricyclic Indoles via Indole Ring Formation

2018

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“…The power of this methodology was also demonstrated by the efficient synthesis of (+ +)-lysergol, [37] an ergot alkaloid which engages various serotonin Gp rotein-coupled receptors, reportedb yL uo and co-workers (Scheme 14). The synthetic advancement toward lysergol began with the chiral alcohol 119,p repared from (R)-Garner's aldehyde by using ap reviously reported method.…”

Section: Scheme9synthesis Of Atorvastatin By Shi and Co-workersmentioning

confidence: 93%

The Expanding Utility of Rhodium‐Iminocarbenes: Recent Advances in the Synthesis of Natural Products and Related Scaffolds

Yang

Zhai

2018

Chemistry A European J

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Rhodium-iminocarbenes that are derived from N-sulfonyl-1,2,3-triazoles have become an important class of reactive species and useful intermediates in organic synthesis. Over the last several years, many practical and versatile approaches involving rhodium-iminocarbene intermediates to synthetically challenging molecules (scaffolds) have been developed. This Minireview mainly summarizes the recent advance of rhodium-iminocarbene involved reactions in the synthesis of natural products and their related scaffolds by the end of 2017. Several applications in important pharmaceuticals are documented as well.

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“…Pinnick oxidation and subsequent esterification to 57 was necessary for the subsequent desilylation using TFA to furnish trisubstituted olefin 67. In the final step, reduction of the ester by DIBAL-H gave the corresponding alcohol 68, from which only two literature-known steps 26 are required to afford (+)-lysergol (56) (Scheme 24).…”

Section: Syn Lettmentioning

confidence: 99%

Cascades Involving anti-Carbopalladation Steps: From Our Initial Hypothesis to Natural Product Synthesis

Schitter¹,

Reding²,

Werz

2019

Synlett

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Our endeavors in the design, realization and application of a formal anti-carbopalladation of alkynes are summarized. Whereas numerous examples of syn-carbopalladation steps embedded in cascade reactions are known, there have been almost no examples of the corresponding anti-carbopalladation steps. From a personal perspective, this account provides insights on the original considerations and hypotheses, and their validation or invalidation by experimental and computational means. This account also aims at clarifying how different ideas have been developed and how novel reaction sequences paving the way to a plethora of different scaffolds have been designed. The reader will recognize the importance of the interplay between elucidating reaction mechanisms and developing novel methodologies. As a result, useful methods to create homo- and heterotetrasubstituted double bonds have been developed. The broad versatility of these methods has been demonstrated by a novel total synthesis of the indole alkaloid (+)-lysergol.1 Introduction2 Initial Studies3 Various Termination Steps4 Termination with Heteronucleophiles5 Natural Product Synthesis6 anti-Carbopalladations Realized by the Lautens Lab7 Conclusion and Outlook

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Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity

Cited by 35 publications

References 55 publications

Synthetic Methods for 3,4‐Fused Tricyclic Indoles via Indole Ring Formation

Synthetic Methods for 3,4‐Fused Tricyclic Indoles via Indole Ring Formation

The Expanding Utility of Rhodium‐Iminocarbenes: Recent Advances in the Synthesis of Natural Products and Related Scaffolds

Cascades Involving anti-Carbopalladation Steps: From Our Initial Hypothesis to Natural Product Synthesis

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